Benzyl chloroformate → 4-Oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester

HRID 1356552노트

반응식

HRID 1356552 반응식
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]1[CH2:26][CH:25]2[CH:21]([CH2:22][CH2:23][C:24]2=[O:27])[CH2:20]1)C1C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]([N:19]1[CH2:26][CH:25]2[CH:21]([CH2:22][CH2:23][C:24]2=[O:27])[CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 10387Benzyl chloroformate2회HCID 134637692-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

생성물 1

HCID 185091484-Oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester수율 72%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Benzyloxycarbonyl chloride (5.14 ml, 36.0 mmol) was added dropwise to a solution of 7-benzyl-2-oxo-7-azabicyclo [3.3.0]octane (5.20 g, 24.2 mmol) in dichloromethane (50 ml) under cooling with ice, followed by stirring at room temperature for 24 hours. The mixture was again cooled with ice, and benzyloxycarbonyl chloride (5.14 ml, 36.0 mmol) was added thereto dropwise. After removing the solvent by evaporation, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4.52 g (17.4 mmol, 72%) of the title compound as acolorless oily substance. 1H-NMR (400 MHz, CDCl3) δ: 1.80-1.90 (1H, m), 2.12-2.22 (1H, m), 2.35-2.39 (2H, m), 2.76 (1H, dt, J=3.5, 8.5 Hz), 3.01-3.11 (1H, m), 3.16-3.26 (1H, m), 3.61-3.66 (1H, m), 3.69-3.78 (1H, m), 5.11-5.12 (2H, m), 7.29-7.38 (5H, m)

후처리

  1. temperatureunder cooling with ice
  2. additionwas added
  3. customAfter removing the solvent
  4. customby evaporation
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-47bacc26ab00498cae97c0adfc3a978b
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586604B2

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